Sodium Hydroxide → HCID 57864027, compound

HRID 1889261Notes

Reaction equation

HRID 1889261 reaction equation
C[O:2][C:3](=[O:31])[C:4]([CH3:30])([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[O:19][CH2:20][CH2:21][CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:23])=[O:8])[CH3:5].[OH-].[Na+]>C1COCC1>[CH3:5][C:4]([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[O:19][CH2:20][CH2:21][CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:23])=[O:8])([CH3:30])[C:3]([OH:31])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 688424952-Methyl-2-{[1-(3-phenyl-butoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester

Product 1

HCID 57864027HCID 57864027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 105 mg 2-methyl-2-{[1-(3-phenyl-butoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester in 2.5 ml THF was treated with 0.2 ml of 2 M aqueous sodium hydroxide. After 3 h at 60° C. another 0.1 ml of 2 M NaOH was added, and after 6 h at 65° C. the reaction was concentrated, the residue was taken up in 3 ml of water, treated with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate and evaporated. After purification by RP-HPLC 15 mg 2-methyl-2-{[1-(3-phenyl-butoxy)-naphthalene-2-carbonyl]-amino}-propionic acid were obtained.

Workup

  1. concentrationafter 6 h at 65° C. the reaction was concentrated
  2. additiontreated with 2 M hydrochloric acid
  3. extractionextracted with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. customevaporated
  6. customAfter purification by RP-HPLC 15 mg 2-methyl-2-{[1-(3-phenyl-butoxy)-naphthalene-2-carbonyl]-amino}-propionic acid
  7. customwere obtained

Sources & evidence

ORD record
ord-c02dee4335614729bebce953302f76bc
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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